"...the journey of crossdressing is like climbing a hill and finding,
upon reaching the top, another, higher hill waiting in the distance. We
are always driven forward by the promise and the mystery of what lies on
the other side."
Over the years, I have avoided for the most part
asking this question of others or trying to answer it for myself. The
reason I steered clear of this one is that trying to answer it can get
in the way of something more important: learning to accept the fact that
we crossdress. I don't want to feel that unless I can explain why, I am
not free to enjoy it.
Before I get too far into this discussion, Id like to clarify what
I mean by the word crossdress.
When I did my on-line survey in 1999, I discovered that only about half
the people who said they crossdressed were actually going to the point
of applying makeup, putting on a wig (or styling their own hair to be
more feminine) and in general present themselves as a woman or trying
The other half crossdress from the neck down.
I am not being judgmental or critical of anyone, and I certainly wont
claim that one approach to crossdressing is better than any other. Everyone
lives with their own sense of what they are comfortable with and what
they can handle.
The reason I mention this is that I sometimes hear crossdressers describe
themselves as typical, normal men
who happen to like
to make themselves look like women. Forgetting for a moment the use of
loaded words like normal, I have to admit to exasperation
with this one. It is, to me, either denial or a vain attempt at having
it both ways. Crossdressers are anything but typical men. We may live
ordinary lives, but we live them in an extraordinary way.
What I do know is this: living almost all of ones life with crossdressing
is an ongoing process of moving between fantasy and reality.
The fantasy is what we think we are capable of, what we think we can
become, who we think we can be. These fantasies become reality by taking
small steps, living now while dreaming about the future. When we are young,
many of us fantasized about being turned into women, through some technology
or magic, or being given the power to transform ourselves back and forth
between male and female at will.
When I was a small child, totally dependent on my parents and with no
control over my own life, I often wondered what it would feel like to
be a girl: to wear my long hair in a pony tail or to have it braided,
to wear dresses and skirts and Mary Jane shoes, to have to walk and sit
and bend down differently.
When I got a little older, I was able to obtain some articles of womens
clothing of my own and try them on. I discovered what it felt like to
dress differently, and in the process what had been only fantasy became
reality. As time went on, I experimented with more clothing, wigs and
makeup and began to develop an image of myself as female, at least in
appearance if nothing else.
This was becoming my reality.
But the journey of crossdressing is like climbing a hill and finding,
upon reaching the top, another, higher hill waiting in the distance. We
are always driven forward by the promise and the mystery of what lies
on the other side.
We all face many of the same hills, some are harder to climb than others.
I remember once, as a teenager, shaving my legs during the summer to
just above the knees. It was both terrifying and exciting because of what
I was both losing and gaining.
I remember another time, going out late at night crossdressed and just
walking around the block in my neighborhood, again terrified of being
caught or even seen by someone, but thrilled by the sensation and the
Sometimes the terror became too great, and out of fear I would turn around
on my path, and decide I didnt want to climb any more hills. I sometimes
felt like I was killing off my male self for the sake of some as of yet
unknown female self. In these times, I would nurture my masculine self.
We call these moments purges and, as we all know, they are
only temporary. In time, we start on our path again.
I was lucky. I never resorted to risky, self-destructive behavior in
an effort to destroy the female in me (by killing off the male host).
I never joined the military, never drank excessively, never used the trappings
of machismo to hurt or punish myself.
But the journeys of many crossdressers are filled with stories like that.
For me it was different. I resorted to sabotage in an effort to destroy
my host. Rather than kill the body, I tried to kill the mind. How did
I do that? By marrying a woman who knew I was a crossdresser and who hated
it. I punished myself with thirteen years of a loveless relationship with
someone who was repulsed by the person I fundamentally was.
And to make sure I suffered, I kept my body alive and well. On the outside,
one might have even thought I was flourishing. Little did they, or I,
know or understand that I had, of my own choice and free will, locked
myself away in a jail cell from which I could see in the far distance,
through a tiny window, the hills I would never allow myself to climb.
But that period of my life is over, and I dont dwell on it. I recall
a line from a popular song I heard when I was a teenager:
Dont let the past remind us of what we
are not now
There were hills to climb and I had wasted too much time already.
But what starts us on this path with these hills? When we are very young,
and we are faced with our first hill, what compels us or motivates us
Is it something in our bodies, some chemical that makes it seem right
to do so? Is it our nature? Or is it the fact that there was no internal
voice telling us not to, no message that says this is not our path? Is
it the way we were nurtured?
Personally, I think it has more to do with how we are brought up than
something organic within our bodies. Children are born perfect, with no
sense of evil, no fear, no notion of what is expected of them. Children
are guiltless, innocent, free. It would only make sense that the longer
a child remains so, the more likely he or she is to experiment with that
same sense of innocence and wonder.
The shame and guilt comes later.
Perhaps there is some biological explanation as well and it is a combination
of biological and environmental factors. How else can you explain the
fact that no one ever chooses to stop, and if they do, its not for
Or perhaps there is no one single explaination for why we do what we
do. Perhaps that's the myopic shortcoming of science: to try to keep everything
else equal and explain human behavior with respect to a single random
variable. Perhaps the very act of answering this question causes the answer
itself to change.
There is, at any rate, something very compelling about crossdressing,
something that makes us want to climb those hills and see whats
on the other side. Our reasons for crossdressing change with time, we
climb new and different hills. I am no longer an eight year old child
wondering. I've climbed that hill and many others.
If you want to understand why you crossdress,
consider the hill you are climbing and what you expect to find at the
And yes, I am aware that I havent answered the question.
Written by Yvonne, a married crossdresser with a supportive partner that
lives in the Albany, New York area. Visit her site at: http://www.yvonnesplace.net
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